DE2535576C2 - Isolongifolen-Derivate und ihre Verwendung - Google Patents
Isolongifolen-Derivate und ihre VerwendungInfo
- Publication number
- DE2535576C2 DE2535576C2 DE2535576A DE2535576A DE2535576C2 DE 2535576 C2 DE2535576 C2 DE 2535576C2 DE 2535576 A DE2535576 A DE 2535576A DE 2535576 A DE2535576 A DE 2535576A DE 2535576 C2 DE2535576 C2 DE 2535576C2
- Authority
- DE
- Germany
- Prior art keywords
- oil
- product
- reaction
- isolongifolene
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- CQUAYTJDLQBXCQ-NHYWBVRUSA-N (-)-isolongifolene Chemical class C([C@@H](C1)C2(C)C)C[C@]31C2=CCCC3(C)C CQUAYTJDLQBXCQ-NHYWBVRUSA-N 0.000 title claims description 17
- 239000000047 product Substances 0.000 description 44
- 239000000203 mixture Substances 0.000 description 35
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 33
- 150000001875 compounds Chemical class 0.000 description 19
- 239000002304 perfume Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 18
- 150000001299 aldehydes Chemical class 0.000 description 17
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 14
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 11
- 150000003138 primary alcohols Chemical class 0.000 description 11
- 150000002576 ketones Chemical class 0.000 description 10
- 150000001298 alcohols Chemical class 0.000 description 9
- -1 terpene compounds Chemical class 0.000 description 9
- 238000010478 Prins reaction Methods 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 239000003205 fragrance Substances 0.000 description 8
- UWKAYLJWKGQEPM-LBPRGKRZSA-N linalyl acetate Chemical compound CC(C)=CCC[C@](C)(C=C)OC(C)=O UWKAYLJWKGQEPM-LBPRGKRZSA-N 0.000 description 8
- 235000016976 Quercus macrolepis Nutrition 0.000 description 7
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 6
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 6
- SUAUILGSCPYJCS-UHFFFAOYSA-N Musk ambrette Chemical compound COC1=C([N+]([O-])=O)C(C)=C([N+]([O-])=O)C=C1C(C)(C)C SUAUILGSCPYJCS-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
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- 235000007769 Vetiveria zizanioides Nutrition 0.000 description 6
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- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 6
- 229960000956 coumarin Drugs 0.000 description 6
- 235000001671 coumarin Nutrition 0.000 description 6
- 235000019253 formic acid Nutrition 0.000 description 6
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 6
- 229940067137 musk ketone Drugs 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 150000003333 secondary alcohols Chemical class 0.000 description 6
- FACFHHMQICTXFZ-UHFFFAOYSA-N 2-(2-phenylimidazo[1,2-a]pyridin-3-yl)ethanamine Chemical compound N1=C2C=CC=CN2C(CCN)=C1C1=CC=CC=C1 FACFHHMQICTXFZ-UHFFFAOYSA-N 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
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- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000001724 (4,8-dimethyl-2-propan-2-ylidene-3,3a,4,5,6,8a-hexahydro-1H-azulen-6-yl) acetate Substances 0.000 description 4
- 241000218645 Cedrus Species 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- UAVFEMBKDRODDE-UHFFFAOYSA-N Vetiveryl acetate Chemical compound CC1CC(OC(C)=O)C=C(C)C2CC(=C(C)C)CC12 UAVFEMBKDRODDE-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- GUUHFMWKWLOQMM-NTCAYCPXSA-N alpha-hexylcinnamaldehyde Chemical compound CCCCCC\C(C=O)=C/C1=CC=CC=C1 GUUHFMWKWLOQMM-NTCAYCPXSA-N 0.000 description 4
- GUUHFMWKWLOQMM-UHFFFAOYSA-N alpha-n-hexylcinnamic aldehyde Natural products CCCCCCC(C=O)=CC1=CC=CC=C1 GUUHFMWKWLOQMM-UHFFFAOYSA-N 0.000 description 4
- 239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 description 4
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 4
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- 239000004615 ingredient Substances 0.000 description 4
- UWKAYLJWKGQEPM-UHFFFAOYSA-N linalool acetate Natural products CC(C)=CCCC(C)(C=C)OC(C)=O UWKAYLJWKGQEPM-UHFFFAOYSA-N 0.000 description 4
- 230000005923 long-lasting effect Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 3
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 3
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 3
- BJIOGJUNALELMI-ONEGZZNKSA-N Isoeugenol Natural products COC1=CC(\C=C\C)=CC=C1O BJIOGJUNALELMI-ONEGZZNKSA-N 0.000 description 3
- 235000019501 Lemon oil Nutrition 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- PDSNLYSELAIEBU-UHFFFAOYSA-N Longifolene Chemical compound C1CCC(C)(C)C2C3CCC2C1(C)C3=C PDSNLYSELAIEBU-UHFFFAOYSA-N 0.000 description 3
- ZPUKHRHPJKNORC-UHFFFAOYSA-N Longifolene Natural products CC1(C)CCCC2(C)C3CCC1(C3)C2=C ZPUKHRHPJKNORC-UHFFFAOYSA-N 0.000 description 3
- 244000179970 Monarda didyma Species 0.000 description 3
- 235000010672 Monarda didyma Nutrition 0.000 description 3
- 240000000513 Santalum album Species 0.000 description 3
- 235000008632 Santalum album Nutrition 0.000 description 3
- 229940007550 benzyl acetate Drugs 0.000 description 3
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- HQKQRXZEXPXXIG-VJOHVRBBSA-N chembl2333940 Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@H]1[C@@](OC(C)=O)(C)CC2 HQKQRXZEXPXXIG-VJOHVRBBSA-N 0.000 description 3
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 3
- BJIOGJUNALELMI-ARJAWSKDSA-N cis-isoeugenol Chemical compound COC1=CC(\C=C/C)=CC=C1O BJIOGJUNALELMI-ARJAWSKDSA-N 0.000 description 3
- 235000000484 citronellol Nutrition 0.000 description 3
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 3
- 239000010648 geranium oil Substances 0.000 description 3
- 235000019717 geranium oil Nutrition 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000000171 lavandula angustifolia l. flower oil Substances 0.000 description 3
- 239000010501 lemon oil Substances 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- 229930007744 linalool Natural products 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 229940067107 phenylethyl alcohol Drugs 0.000 description 3
- 239000010671 sandalwood oil Substances 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- 235000007586 terpenes Nutrition 0.000 description 3
- BJIOGJUNALELMI-UHFFFAOYSA-N trans-isoeugenol Natural products COC1=CC(C=CC)=CC=C1O BJIOGJUNALELMI-UHFFFAOYSA-N 0.000 description 3
- 239000010679 vetiver oil Substances 0.000 description 3
- VPKMGDRERYMTJX-CMDGGOBGSA-N 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one Chemical compound CCC(=O)\C=C\C1C(C)=CCCC1(C)C VPKMGDRERYMTJX-CMDGGOBGSA-N 0.000 description 2
- INIOTLARNNSXAE-UHFFFAOYSA-N 4,8-dimethyl-2-propan-2-ylidene-3,3a,4,5,6,8a-hexahydro-1h-azulen-6-ol Chemical compound CC1CC(O)C=C(C)C2CC(=C(C)C)CC12 INIOTLARNNSXAE-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- ZCTQGTTXIYCGGC-UHFFFAOYSA-N Benzyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 2
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- 239000005770 Eugenol Substances 0.000 description 2
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- 241000208152 Geranium Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
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- 240000005385 Jasminum sambac Species 0.000 description 2
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- CRZQGDNQQAALAY-UHFFFAOYSA-N Methyl benzeneacetate Chemical compound COC(=O)CC1=CC=CC=C1 CRZQGDNQQAALAY-UHFFFAOYSA-N 0.000 description 2
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- KVWWIYGFBYDJQC-GHMZBOCLSA-N Methyl dihydrojasmonate Chemical compound CCCCC[C@@H]1[C@@H](CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-GHMZBOCLSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
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- 229940062909 amyl salicylate Drugs 0.000 description 2
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- SVURIXNDRWRAFU-OGMFBOKVSA-N cedrol Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@@H]1[C@@](O)(C)CC2 SVURIXNDRWRAFU-OGMFBOKVSA-N 0.000 description 2
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- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- GLZPCOQZEFWAFX-JXMROGBWSA-N Nerol Natural products CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 235000001466 Ribes nigrum Nutrition 0.000 description 1
- 241001312569 Ribes nigrum Species 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 244000178231 Rosmarinus officinalis Species 0.000 description 1
- 235000005212 Terminalia tomentosa Nutrition 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000001408 angelica archangelica l. root oil Substances 0.000 description 1
- 235000001053 badasse Nutrition 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000010627 cedar oil Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 1
- 229940117916 cinnamic aldehyde Drugs 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- 229930003633 citronellal Natural products 0.000 description 1
- 235000000983 citronellal Nutrition 0.000 description 1
- 239000001071 citrus reticulata blanco var. mandarin Substances 0.000 description 1
- 239000010633 clary sage oil Substances 0.000 description 1
- 239000010634 clove oil Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 229930008394 dihydromyrcenol Natural products 0.000 description 1
- XSNQECSCDATQEL-UHFFFAOYSA-N dihydromyrcenol Chemical compound C=CC(C)CCCC(C)(C)O XSNQECSCDATQEL-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229940095104 dimethyl benzyl carbinyl acetate Drugs 0.000 description 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 229940073505 ethyl vanillin Drugs 0.000 description 1
- 229940093468 ethylene brassylate Drugs 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000001148 ferula galbaniflua oil terpeneless Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000001927 guaiacum sanctum l. gum oil Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229930002839 ionone Natural products 0.000 description 1
- 150000002499 ionone derivatives Chemical class 0.000 description 1
- 244000056931 lavandin Species 0.000 description 1
- 235000009606 lavandin Nutrition 0.000 description 1
- 239000001102 lavandula vera Substances 0.000 description 1
- 235000018219 lavender Nutrition 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910001641 magnesium iodide Inorganic materials 0.000 description 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
- 229940102398 methyl anthranilate Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XMWRWTSZNLOZFN-UHFFFAOYSA-N musk xylene Chemical group CC1=C(N(=O)=O)C(C)=C(N(=O)=O)C(C(C)(C)C)=C1N(=O)=O XMWRWTSZNLOZFN-UHFFFAOYSA-N 0.000 description 1
- 239000001627 myristica fragrans houtt. fruit oil Substances 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 239000001622 pimenta officinalis fruit oil Substances 0.000 description 1
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229930007790 rose oxide Natural products 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/28—Saturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
- C07C47/34—Saturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings polycyclic
- C07C47/347—Saturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings polycyclic having a —CHO group on a condensed ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/38—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
- C07C47/44—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings polycyclic
- C07C47/445—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings polycyclic containing a condensed ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/29—Saturated compounds containing keto groups bound to rings
- C07C49/313—Saturated compounds containing keto groups bound to rings polycyclic
- C07C49/323—Saturated compounds containing keto groups bound to rings polycyclic having keto groups bound to condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
- C07C49/553—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings polycyclic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Disinfection, Sterilisation Or Deodorisation Of Air (AREA)
- Chemical Or Physical Treatment Of Fibers (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB35244/74A GB1519443A (en) | 1974-08-09 | 1974-08-09 | Isolongifolene derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2535576A1 DE2535576A1 (de) | 1976-02-26 |
| DE2535576C2 true DE2535576C2 (de) | 1985-12-19 |
Family
ID=10375522
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2535576A Expired DE2535576C2 (de) | 1974-08-09 | 1975-08-08 | Isolongifolen-Derivate und ihre Verwendung |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4100110A (enrdf_load_stackoverflow) |
| JP (1) | JPS6159285B2 (enrdf_load_stackoverflow) |
| CH (1) | CH621105A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2535576C2 (enrdf_load_stackoverflow) |
| GB (1) | GB1519443A (enrdf_load_stackoverflow) |
| NL (1) | NL186084C (enrdf_load_stackoverflow) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI780440A7 (fi) | 1978-01-12 | 1979-07-13 | Unilever Nv | Detergentkomposition |
| FI780439A7 (fi) | 1978-01-12 | 1979-07-13 | Unilever Nv | Tvaettmedel |
| US4288341A (en) | 1978-03-20 | 1981-09-08 | Lever Brothers Company | Detergent product containing deodorant compositions |
| EP0339299B1 (fr) * | 1988-04-27 | 1994-11-30 | Firmenich Sa | Ester bicyclique odorant |
| US5851180A (en) * | 1996-07-12 | 1998-12-22 | United States Surgical Corporation | Traction-inducing compression assembly for enhanced tissue imaging |
| DE10038544A1 (de) * | 2000-08-03 | 2002-02-14 | Dragoco Gerberding Co Ag | Isolongifolenylether, ihre Herstellung und ihre Verwendung |
| ES2388461T3 (es) * | 2005-09-14 | 2012-10-15 | Givaudan Sa | Compuestos terpenoides tricíclicos o tetracíclicos que contienen oxígeno |
| WO2007079466A2 (en) * | 2006-01-04 | 2007-07-12 | Nano Mist International, Llc | Air driven delivery system for sprayable media |
| US7579016B2 (en) * | 2007-07-13 | 2009-08-25 | The United States Of America As Represented By The Secretary Of Agriculture | Methods for repelling arthropods using isolongifolenone analogs |
| CN103951566B (zh) * | 2014-04-30 | 2015-06-17 | 南京林业大学 | 一种N-烃基-1,2,3,4,5,6-六氢-1,1,5,5-四甲基-7H-2,4α-桥亚甲基萘-7-胺类化合物及其合成方法和应用 |
| CN112624920B (zh) * | 2019-09-24 | 2023-08-29 | 北京藏卫信康医药研发有限公司 | 4-棕榈酰氧基-2-甲基-2-丁烯醛的合成方法、及维生素a棕榈酸酯的合成方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1152995A (en) * | 1965-11-26 | 1969-05-21 | May & Baker Ltd | New Formate Esters |
| DE1913691A1 (de) * | 1968-03-21 | 1969-11-06 | Bush Boake Allen Ltd | Parfuemeriezusammensetzungen |
| GB1256535A (enrdf_load_stackoverflow) * | 1968-09-27 | 1971-12-08 | ||
| US3718698A (en) * | 1969-11-24 | 1973-02-27 | Int Flavors & Fragrances Inc | Isolongifolene processes and product |
| US3799987A (en) * | 1971-01-18 | 1974-03-26 | Givaudan Corp | 4-acetic-6,8a-ethano-1,1,6-trimethyl-1,2,3,5,6,7,8,8a-octahydronaphthalene, process for making same and compositions containing same |
| GB1434035A (en) * | 1972-07-20 | 1976-04-28 | Naarden International Nv | Process for the preparation of sesquiterpene ketones |
| GB1505821A (en) * | 1975-04-01 | 1978-03-30 | Bush Boake Allen Ltd | Isolongifolene derivatives and their use in perfumery compositions |
-
1974
- 1974-08-09 GB GB35244/74A patent/GB1519443A/en not_active Expired
-
1975
- 1975-08-08 DE DE2535576A patent/DE2535576C2/de not_active Expired
- 1975-08-08 CH CH1039875A patent/CH621105A5/de not_active IP Right Cessation
- 1975-08-08 NL NLAANVRAGE7509476,A patent/NL186084C/xx not_active IP Right Cessation
- 1975-08-09 JP JP50097115A patent/JPS6159285B2/ja not_active Expired
- 1975-08-11 US US05/603,908 patent/US4100110A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NL186084B (nl) | 1990-04-17 |
| JPS6159285B2 (enrdf_load_stackoverflow) | 1986-12-16 |
| GB1519443A (en) | 1978-07-26 |
| JPS5143751A (enrdf_load_stackoverflow) | 1976-04-14 |
| CH621105A5 (enrdf_load_stackoverflow) | 1981-01-15 |
| US4100110A (en) | 1978-07-11 |
| AU8385075A (en) | 1977-02-17 |
| NL186084C (nl) | 1990-09-17 |
| NL7509476A (nl) | 1976-02-11 |
| DE2535576A1 (de) | 1976-02-26 |
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Legal Events
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Representative=s name: BERENDT, T., DIPL.-CHEM. DR., PAT.-ANW., 8000 MUEN |
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| 8110 | Request for examination paragraph 44 | ||
| 8128 | New person/name/address of the agent |
Representative=s name: SCHMIED-KOWARZIK, V., DR., 8000 MUENCHEN DANNENBER |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |